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Contents:
What is Thionyl Chloride? Preparation Method Of Thionyl Chloride
Applications
MSDS What is Sulfuryl Chloride?
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Often confused with sulfuryl chloride. Miscible with CCl3,benzene etc. Pyramidal lone pair of electrons at
the top
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Preparation Methods
1. Oldest methods of thionyl chloride preparation : reacting PCl5 and SO2
(Scheme 1)
Schudel, J. G.; United States Patent Office, 1931. (No 1.788.959)
2. Hallowell and Vaalas process: SO2 and CCl4 or CHCl3, and a Friedel-
Crafts catalyst,extreme temperatures (140 to 400 C) and pressure (15 to 200 atm) (Scheme2).
Hallowell, A. T.; Vaala, G. T.; United States Patent Office, 1946. (No 2.393.247)5 6-Nov-13
Using sulfur chloride (SCl2), Cl2, and sulfuric acid (H2SO4), drawbacks are the
formation of SO2 and hydrochloric acid (HCl) (Scheme 4)
Pechkas, A.; United States Patent Office, 1947. (No 2.431.823)
Reacting SO2, Cl2 and S2Cl2 or SCl2, activated carbon as catalyst (Scheme 5).
SO2, Cl2 and different carbon sources (e.g., wood, bone, coal, and sugar), containing
activated metals after treatment with hydrochloric acid as a catalyst, SO2can be produced in good yields (Scheme 6).
Cicha, W. V.; Manzer, L. E.; United States Patent Office, 1999. (No 5.879.652) 6-Nov-13 6
John E. Hill proposed an integrated process that reuses waste from other manufacturing
processes and monitors the steps of the industrial production of SOCl2
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Applications
The most common uses of Thionyl Chloride in chemistry are: the production of acyl chloride and sulfuryl chloride,using the corresponding
carboxylic acids and sulphonic acids as a raw material.
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Mechanism:
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As a condensing agent: Acetanilides react with dialkylformamides 401 in the presence of thionyl
chloride as a condensing agent to give the formamidines 402, which are used as acaricides and/or insecticides
Formation of sulfides:
Chlorination: The mechanism by which thionyl chloride acts as a chlorinating agent is not fully
understood. One possible explanation is that thionyl chloride undergoes oxidation in the presence of atmospheric oxygen to sulfuryl chloride, which is a well known chlorinating agent for organic substances
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MSDS
Very hazardous in case of skin contact (irritant, corrosive, permeator), of eye
contact (irritant, corrosive), of ingestion, of inhalation. Skin contact may produce burns. membranes of eyes, mouth and respiratory tract.
Precautions:
Keep container dry. Keep away from heat ,sources of ignition, direct sunlight or strong
incandescent light.
Do not ingest/ breathe gas/fumes/ vapour/spray. Never add water to this product. Avoid shock and friction. Keep away from incompatibles such as metals, acids, alkalis, moisture.
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Storage:
Keep container tightly closed. Keep container in a cool. Keep in a well-ventilated area. Note:
It will explode in presence of severalchemicals:Azidoacetylacid,Chlorylperchlorate, N,N-Dimethylformaide,Dimethylsulfoxide etc.
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Preparation Methods
It is prepared by the reaction of sulfur dioxide and chlorine in the presence
of a catalyst, such as activated carbon.
The crude product can be purified by fractional distillation. It is uncommon to prepare SO2Cl2 in the laboratory because it is
commercially available.
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Applications
It is used as a chlorinating and sulfonating agent. Acylation of alcohols and amines, the conversion of carboxylic acid salts to
acid chlorides and anhydrides
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Silberrad, O., Silberrad, C. A., and Parke, B., Ibki., 127, 1724
Asymmetric Catalysis: The given Diol is converted into protected amino group using
sulfuryl chloride and this also be done using thionyl chloride.
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MSDS
Extremely hazardous in case of skin contact (corrosive, irritant, sensitizer),
of eye contact (irritant), of ingestion, of inhalation.
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Precaution
Keep container dry. Do not breathe gas/fumes/ vapour/spray.
References:
Schudel, J. G.; United States Patent Office, 1931. (No 1.788.959) Hallowell, A. T.; Vaala, G. T.; United States Patent Office, 1946. (No
2.393.247)
Pechkas, A.; United States Patent Office, 1947. (No 2.431.823) Cicha, W. V.; Manzer, L. E.; United States Patent Office, 1999. (No
5.879.652)
Industrial Preparation Methods of Chemical Solvents and Reagents Virtual Journal of Chemistry ISSN 1984-6835 Volume XX Issue XX
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